Chlorine → HCID 21531119, compound

HRID 1657920Notes

Reaction equation

HRID 1657920 reaction equation
[Br:1][C:2]1[C:3]([Cl:12])=[C:4]([CH:7]=[CH:8][C:9]=1[CH2:10][CH3:11])[CH2:5][Cl:6].[Cl:13]Cl>C(Cl)Cl.[Fe]>[Br:1][C:2]1[C:3]([Cl:12])=[C:4]([CH:7]=[C:8]([Cl:13])[C:9]=1[CH2:10][CH3:11])[CH2:5][Cl:6].[Br:1][C:2]1[C:3]([Cl:12])=[C:4]([C:7]([Cl:13])=[CH:8][C:9]=1[CH2:10][CH3:11])[CH2:5][Cl:6]

Participants

6

Reactant 2

HCID 24526ChlorineHCID 21531067HCID 21531067, compound

Product 2

HCID 21531119HCID 21531119, compoundHCID 21531207HCID 21531207, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 54 parts of 3-bromo-2-chloro-4-ethylbenzyl chloride and 3 parts of iron filings at 90°-95°C is treated with chlorine in the absence of light until there is no additional gain in weight, then cooled and diluted with methylene chloride. The mixture is filtered, and the filtrate is washed with water and dilute sodium bisulfite, then dried and concentrated. The residue is chromatographed and 3-bromo-2,5-dichloro-4-ethylbenzyl chloride and a small amount of 3-bromo-2,6-dichloro-4-ethylbenzyl chloride are isolated as two of the fractions.

Workup

  1. temperaturecooled
  2. filtrationThe mixture is filtered
  3. washthe filtrate is washed with water and dilute sodium bisulfite
  4. customdried
  5. concentrationconcentrated
  6. customThe residue is chromatographed

Sources & evidence

ORD record
ord-6af3dfaa339845d3a80d5aafc84c7320
Source dataset
uspto-grants-1976_06
Patent number
US03962307

Reaction notes

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